Potassium Carbonate → Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

HRID 14002

反応式

HRID 14002 の反応式
[CH2:1](B(O)O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+].Br[C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[C:25]([C:23]1[CH:22]=[C:17]([CH:16]=[C:15]([CH2:1][CH3:2])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:26])[CH2:29][CH3:30]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 521157Ethylboronic acidHCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

生成物 1

HCID 22593628Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 g, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture is heated at 100 degrees C. for 18 hours. The mixture is then partitioned between ethyl acetate and water. The phases are separated and the ethyl acetate phase is washed with saline, dried over sodium sulfate and concentrated. The concentrate is column chromatographed (silica gel; ethyl acetate/hexanes, 15/85) to give the title compound, MS (ESI+) for C17H25NO3 m/z (M+H)+=292.2.

後処理

  1. customThe mixture is then partitioned between ethyl acetate and water
  2. customThe phases are separated
  3. washthe ethyl acetate phase is washed with saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (silica gel; ethyl acetate/hexanes, 15/85)

出典と根拠

ORDレコード
ord-87b264a8e2c347b0ba0c3634ea5dddab
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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